Title: Palitantin
CAS Registry Number: 15265-28-8
CAS Name: (2R,3S,5R,6R)-rel-3-(1E,3E)-1,3-Heptadienyl-5,6-dihydroxy-2-(hydroxymethyl)cyclohexanone
Molecular Formula: C14H22O4
Molecular Weight: 254.32
Percent Composition: C 66.12%, H 8.72%, O 25.16%
Literature References: Metabolic product of Penicillium palitans Westling. Isoln: J. H. Birkinshaw, H. Raistrick, Biochem. J. 30, 801 (1936). Derivs and degradation products: J. H. Birkinshaw, ibid. 51, 271 (1952). Structure: K. Bowden et al., J. Chem. Soc. 1959, 1662. Biosynthesis: P. Chaplen, R. Thomas, Biochem. J. 77, 91 (1960); A. J. Birch, M. Kocor, J. Chem. Soc. 1960, 866. Reactivity studies: A. T. Austin, B. Pearson, Chem. Ind. (London) 1966, 1228. Stereoselective synthesis of (±)-form: A. Ichihara et al., Tetrahedron Lett. 1977, 3473; eidem, Tetrahedron 36, 1547 (1980).
Properties: Needles from hot water, mp 165°. [a]235461 +4.4° (c = 0.8 in CHCl3). uv max (ethanol): 323 nm (e 34,000). Sol in hot water, alc, chloroform; slightly sol in cold water, ether.
Melting point: mp 165°
Optical Rotation: [a]235461 +4.4° (c = 0.8 in CHCl3)
Absorption maximum: uv max (ethanol): 323 nm (e 34,000) |